When you need to dynamically display a block within a region, nothing can really beat the Context module. It allows you to define a set of conditions, that when met, executes a set of reactions. For example, you could create a context rule which adds a block to the sidebar second region (reaction) when a user is viewing an Article content type (condition).
A lot of what Context does can also be achieved using Panels. But if you're new to Drupal, and never used Panels than Context will be...